HCID 86717460, compound → HCID 86717461, compound

HRID 712001Notes

Reaction equation

HRID 712001 reaction equation
[C:1]([O:4][CH2:5][CH:6]([O:9][CH2:10][C@@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH2:13])C=C)(=[O:3])[CH3:2]>C(=[Ru](Cl)(Cl)([C-]1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][CH:6]1[CH:13]=[CH:12][C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:10][O:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86717460HCID 86717460, compound

Product 1

HCID 86717461HCID 86717461, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 178425457HCID 178425457, compoundCatalyst

Procedure

To a 500 mL 2-neck round bottom flask, benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)ruthenium (38 mg, 0.044 mmol) was added. After purged with nitrogen for 3 times, dichloromethane (anhydrous, 8 mL) was added followed by 2-({(2S)-2-[(tert-butoxycarbonyl)amino]but-3-en-1-yl}oxy)but-3-en-1-yl acetate (265 mg, 0.885 mmol). The reaction mixture was stirred at room temperature for 15 h. The mixture was concentrated in vacuo. The residue was purified via flash chromatography (eluting with hexanes to 25% EtOAc in hexanes) to give the desired product as a brown oil (0.205 g, 85%). LCMS calculated for C9H14NO5 (M+H-Bu+H)+: m/z=216.1. Found: 216.1. 1H NMR (300 MHz, CDCl3) δ 5.94 (0.17H, m), 5.84 (0.83H, m), 5.69 (1H, m), 4.89 (0.13H, m), 4.70 (0.83H, m), 4.25 (1H, m), 4.05 (4H, m), 3.56 (0.13H, m), 3.38 (0.87H, m), 2.04 (2.49H, s), 2.03 (0.51H, m), 1.38 (9H, s) ppm (The product was a ˜5:1 mixture of trans- and cis-isomers).

Workup

  1. customAfter purged with nitrogen for 3 times, dichloromethane (anhydrous, 8 mL)
  2. additionwas added
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was purified via flash chromatography (eluting with hexanes to 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-acec4cde13654fb68ae2fa049c74920e
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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